16 Classic Fall Dates, Best vs. Worst Case Scenarios

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Fall is here, and we’re thrilled. We’re snatching up all the cutest fall sweaters, we’ve been planning our Halloween costume for months, and we don’t need an excuse to indulge in pumpkin spice lattes.

We’re also pumped for fall date activities. No need to worry about your bikini body, or sweating under the summer sun, or falling for someone who’s only in town for a brief summer vacation. Autumn means apple picking and cuddling under cozy blankets and borrowing his Patagonia. Cuffing season is real, and it’s here, and we’re ready for it.

Unfortunately for all of us, dates don’t always go as planned. And as picture perfect as all these fall activities seem on paper, they don’t always quite pan out that well. Before you embark on an autumn adventure, prepare yourself for the worst case scenario. Hey, if you set your standards low, then your expectations can only be exceeded, right?

1. Going apple picking


Best Case: You’ll be in the middle of an idyllic, old school farm, surrounded by fragrant apple trees and baby goats. There will be freshly baked apple cider donuts and warm apple cider. You’ll hold hands as you stroll through the orchard with your sack full of fruit.

Worst Case: The baby goats will smell bad, and one will chew the hem of your chunky knit sweater. Half of the apples will already be rotten. You’ll burn your tongue on the much-too-hot apple cider, and even if you still want to make out with your date (after they jokingly threw an apple at you that actually really hurt), you won’t be able to enjoy it.